Organometallic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-2016204362-A1
Application number	US-201514931270-A
Country	US
Kind code	A1
Filing date	Nov 3, 2015
Priority date	Jan 9, 2015
Publication date	Jul 14, 2016
Grant date	—

Abstract

An organometallic compound represented by Formula 1:

wherein in Formula 1, groups and variables are the same as described in the specification.

First claim

What is claimed is:

1 . An organometallic compound represented by Formula 1:

wherein in Formula 1,
M is selected from a Period 1 transition metal, a Period 2 transition metal, and a Period 3 transition metal;
A 11 to A 13 are each independently selected from a C 6 -C 20 cyclic group and a C 1 -C 20 heterocyclic group; wherein A 11 and A l2 are optionally linked to each other through a first linking group;
X 11 to X 13 are each independently selected from C and N;
X 14 is selected from N and P;
E 11 to E 14 and Y 11 to Y 15 are each independently selected from a single bond and a divalent linking group; X 14 and Y 14 are linked together by a single bond or a double bond, and X 14 and Y 15 are linked together by a single bond or a double bond;
L 11 is selected from a monodentate ligand and a bidentate ligand;
a11 is selected from 0, 1, and 2; and
R 11 to R 13 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —C(═O)(Q 1 ), —Si(Q 1 )(Q 2 )(Q 3 ), and —N(Q 1 )(Q 2 );
wherein Q 1 to Q 3 are each independently selected from a C 1 -C 60 alkyl group and a C 6 -C 60 aryl group;
b11 to b13 are each independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10; and
at least one substituent of the substituted C 1 -C 60 alkyl group, substituted C 2 -C 60 alkenyl group, substituted C 2 -C 60 alkynyl group, substituted C 1 -C 60 alkoxy group, substituted C 3 -C 10 cycloalkyl group, substituted C 1 -C 10 heterocycloalkyl group, substituted C 3 -C 10 cycloalkenyl group, substituted C 1 -C 10 heterocycloalkenyl group, substituted C 6 -C 60 aryl group, substituted C 6 -C 60 aryloxy group, substituted C 6 -C 60 arylthio group, substituted C 1 -C 60 heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic condensed heteropolycyclic group is selected from
a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof; and
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

2 . The organometallic compound of claim 1 , wherein
M is selected from Os, Ir, and Pt.

3 . The organometallic compound of claim 1 , wherein
A 11 to A 13 are each independently selected from a benzene, a naphthalene, a fluorene, an indene, a furan, a thiophene, a carbazole, a benzofuran, a benzothiophene, a dibenzofuran, a dibenzothiophene, a pyrrole, an imidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, an isoxazole, an oxadiazole, a triazole, a pyridine, a pyrimidine, a pyrazine, a pyridazine, a triazine, a quinoline, an isoquinoline, a quinoxaline, a quinazoline, an indole, a benzoimidazole, a benzoxazole, an isobenzoxazole, an indazole, and a tetrahydroindazole; and a benzene, a naphthalene, a fluorene, an indene, a furan, a thiophene, a carbazole, a benzofuran, a benzothiophene, a dibenzofuran, a dibenzothiophene, a pyrrole, an imidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, an isoxazole, an oxadiazole, a triazole, a pyridine, a pyrimidine, a pyrazine, a pyridazine, a triazine, a quinoline, an isoquinoline, a quinoxaline, a quinazoline, an indole, a benzoimidazole, a benzoxazole, an isobenzoxazole, an indazole, and a tetrahydroindazole, each condensed with at least one selected from a C 4 -C 10 alicyclic group and a C 1 -C 10 heteroalicyclic group.

4 . The organometallic compound of claim 1 , wherein
A 11 is selected from groups represented by Formulae 2-1 to 2-8:

wherein in Formulae 2-1 to 2-8,
* is a binding site to M or E 11 in Formula 1;
*′ is a binding site to Y 11 or Y 13 ; and
R 21 to R 25 each independently are the same as R 11 in Formula 1.

5 . The organometallic compound of claim 1 , wherein
A l2 and A 13 are each independently selected from groups represented by Formulae 3-1 to 3-9:

wherein in Formulae 3-1 to 3-9,
* is a binding site to M, E 12 , or E 13 in Formula 1;
*′ is a binding site to Y 11 or Y 12 ; and
R 31 to R 40 each independently are the same as R 12 and R 13 in Formula 1.

6 . The organometallic compound of claim 1 , wherein
X 14 is N.

7 . The organometallic compound of claim 1 , wherein
Y 11 to Y 15 are each independently selected from a single bond, a double bond, —O—, —S—, —{B(Q 11 )}-, —{N(Q 12 )}-, —{C(Q 11 )(Q 12 )} n11 -, ═{C(Q 11 )} n1 -, —{Si(Q 11 )(Q 12 )} n11 -, —C(═O)—, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group; wherein Q 11 and Q 12 are each independently selected from a hydrogen, a deuterium, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, and a C 1 -C 60 heteroaryl group; and n11 is selected from 1, 2, and 3.

8 . The organometallic compound of claim 1 , wherein
Y 11

Assignees

• Samsung Electronics Co Ltd

Inventors

• Park Bumwoo
• Kwak Yoonhyun
• Koo Hyun
• Kim Jiwhan
• Lee Sunyoung
• Lee Jiyoun

Classifications

• H01L51/0085

  Electricity · mapped topic

• H01L51/5012

  Electricity · mapped topic

• C07F15/0033

  Iridium compounds · CPC title

• C07F15/0086 Primary

  Platinum compounds · CPC title

• C07F15/0093

  without a metal-carbon linkage · CPC title